[Heli0x]

Hi everyone.

I'm having difficulty drawing the resonance forms of 2-Naphthole. The first step is what confuses me:

If the double bond on the second ring goes from position 1 to position 2 (also where the OH is located), then where would the lone pair be located if I choose to create a double bond from one lone pair from the OH? That would make a total of 4 bonds+1 lone pair on the carbon which is impossible.

Also, I have some issues drawing the resonance for a simple phenol. The last step is somewhat weird.

What can be done??

Picture of the two problems:

http://img80.imageshack.us/img80/9092/resonansphenol.png (Ignore the "+" on the top right oxygen, last one).

[sjb]

If you're pushing a lone pair from the oxygen onto the ipso carbon, then the electrons from the double bond at that carbon can formally at least move to the carbon at 12 o'clock, just like you've drawn for your first two resonance structures for phenol, above

[Heli0x]

I'm not familiar with them term "ipso" (haven't studied that much org-chem yet), but what about the rest of the forms?

And more importantly, what about the 2-Naphthol?

[sjb]

Sorry, I merely meant the carbon that has the (former) OH group bonded to it.

[Heli0x]

Oh ok, thanks.

I'm sorry if keep nagging you, but do you have any comments on the rest? Where I'm going wrong so to speak.

[sjb]

Your first four structures look fine. I'm not convinced by the arrows on structure 4, though. If you push the negative charge from the atom at 10 o'clock onto the carbon at 12, then the only place you can move electrons without breaking up the ring is up to the oxygen, reforming a neutral, non-zwitterionic phenol, with the structure formally at least a mirror of the very first structure.

[Heli0x]

Hmm ok.

What about the 2-Naphthole, am I supposed to completely remove the H-atom and then draw resonance?

[sjb]

Hmm ok.

What about the 2-Naphthole, am I supposed to completely remove the H-atom and then draw resonance?

No, remember resonance structures only differ in the arrangment of electrons, not nuclei

[Heli0x]

Ok.

How should I start the resonance form then? Having trouble with the initiating step so to speak.